Dimethylformamide → HCID 131718111、化合物

HRID 5063ノート

反応式

HRID 5063 の反応式
[CH3:1][C:2]1[O:6][C:5](=[O:7])[O:4][C:3]=1[CH2:8]I.[O:10]=[C:11]1[CH:15]([S:16][C:17]2[C@H:18]([CH3:31])[C@@H:19]3[C@@H:26]([C@H:27]([OH:29])[CH3:28])[C:25](=[O:30])[N:20]3[C:21]=2[C:22]([O-:24])=[O:23])[CH2:14][CH2:13][NH:12]1.[Na+].CN(C)C=O>C(Cl)(Cl)Cl.C(OCC)(=O)C>[O:10]=[C:11]1[CH:15]([S:16][C:17]2[C@H:18]([CH3:31])[C@@H:19]3[C@@H:26]([C@H:27]([OH:29])[CH3:28])[C:25](=[O:30])[N:20]3[C:21]=2[C:22]([O:24][CH2:8][C:3]2[O:4][C:5](=[O:7])[O:6][C:2]=2[CH3:1])=[O:23])[CH2:14][CH2:13][NH:12]1

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 189421374-(Iodomethyl)-5-methyl-2H-1,3-dioxol-2-oneHCID 131718112HCID 131718112、化合物

生成物 1

HCID 131718111HCID 131718111、化合物収率 45.7%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 66 mg of 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl iodide (prepared by heating 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide and sodium iodide under reflux in acetone) in chloroform was added to a mixture of 47.6 mg of sodium (1R, 5S, 6S)-2-(2-oxo-3-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate and 0.4 ml of dry dimethylformamide. The mixture was stirred at room temperature for 80 minutes and then at 30°-45° C. for 4.5 hours. At the end of this time, the reaction mixture was diluted with ethyl acetate and washed four times with an aqueous solution of sodium chloride. The extract was dried and the solvent was distilled off under reduced pressure. The residue was purified by Lobar column chromatography (Merck, LiChroprep Si60, size A), eluted with a 10:1 by volume mixture of ethyl acetate and methanol, to give 27.4 mg of the title compound in the form of a colorless powder.

後処理

  1. waitat 30°-45° C. for 4.5 hours
  2. washwashed four times with an aqueous solution of sodium chloride
  3. customThe extract was dried
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by Lobar column chromatography (Merck, LiChroprep Si60, size A),
  6. washeluted with a 10:1 by volume mixture of ethyl acetate and methanol

出典と根拠

ORDレコード
ord-d17197b3300b4c588249b50f58b34560
出典データセット
uspto-grants-1993_09
特許番号
US05242914

反応ノート

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